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Weinstein was one of the founding writers/performers of the show in 1988 at the age of 17. Weinstein worked on Mystery Science Theater 3000 during its original appearance on Minneapolis UHF station KTMA-TV from 1988 to 1989, and its first season on Comedy Central (then called the Comedy Channel) from 1989 to 1990. However, a significant age gap existed between him and the other cast members; he was only 17 when he joined the show, having been recruited by Joel from his "Creative Stand-Up and Smartology" comedy classes. This ultimately led to Weinstein feeling unhappy with the more professional approach to the show the move to the Comedy Channel demanded, and caused him to leave the show.[2]

Weinstein has an extensive background in stand-up comedy; he has performed over a thousand shows as a stand-up comedian, and has also written material for Garry Shandling, Dennis Miller, Roseanne Barr, Louie Anderson and other comedians. He is currently the president of Stinkburger Inc.[6]